Benzoyl benzoic ester plasticized composition



Patented Dec. 20, 1938 BENZOYL BENZOIC ESTER PLASTICIZED COMPOSITIONHerbert A. Winkelmann, Chicago, 111., assignor to Marbon Corporation,Chicago, 111., a corporation of Delaware No Drawing. ApplicationDecember 30, 1936, Serial No. 118,324

3 Claims. (Cl. 106-23) This invention relates to plastic and coatingrubber hydrochloride is butyl benzoyl benzoate. compositions and, moreparticularly, relates to All the compounds within this class of estersof such compositions comprising a halogen oontainbenzoyl benzoic acidare practically non-volatile ing rubber derivative and a plasticizertherefor. at ordinary atmospheric temperature and pres- The halogencontaining rubber derivatives sure, are sufiiciently compatible with thehalogen 5 such as chlorinated rubber, rubber hydrochlocontaining rubberderivatives to serve as plastiride, chlorinated rubber hydrochlorides,and cizers, and are readily incorporated in plastics. vulcanized rubberhydrochlorides are suitable The proportion of these plasticizers to beinfor use in coating and plastic compositions and corporated with thehalogen containing rubber for some purposes do not require modifyingderivative will depend, of course, toalarge extent 10 agents. For manypurposes, however, it is on the properties desired in the resultingcompohighly advantageous to use these substances in sition and on thenature of the halogen containconnection with a plasticizer, i. e., asubstance ing rubber derivative. Preferably the plasticizer ofnegligibly low volatility and which dissolves will be present in fromabout 10 to 50% by weight or is dissolved by the halogen containingrubof the amount of halogen containing rubber de- 15 her derivative torender the composition less rivative present. Where great pliability isdesired brittle and more supple than it would otherthe proportion may befrom 50 to 100%. wise be. The esters of benzoyl benzoic acid are par-All the halogen containing rubber derivatives ticularly valuableplasticizers for vulcanized rubare not efiected the same byplasticizers. In her hydrochlorides. The hot vulcanization of 20 generalthe chlorinated rubbers are readily plasrubber hydrochlorides with minorproportions ticized by a large number of materials, the of sulfur andaccelerator produces a relatively amorphous rubber hydrochlorides arealso readsoft, elastic, flexible composition which, howily plasticized,the crystalline saturated rubber ever, has a slight tendency to set upor harden hydrochlorides, particularly the highly insoluble with age.The esters of benzoyl benzoic acid 25 type, are more difiicult toplasticize and the vulhave the important property of not deleteriouslycanized rubber hydrochlorides, in general, the effecting thevulcanization of rubber hydromost diflicult of all. halides when presentin the rubber hydrohalide- I have discovered that the esters of benzoylsulfur composition, and of plasticizing the vulbenzoic acid are ingeneral good plasticizers for canized rubber hydrochlorides so that theywill 30 all the halogen containing rubber derivatives inremain soft andsupple. These properties are cluding the vulcanized rubberhydrochlorides. present in only a few out of a large number of It hasbeen found that the benzoates of the nonvolatile organic materialstested. class given above are compatible with the halo- In order toillustrate the invention, the folgen containing rubber derivatives, atleast to a lowing examples are given, parts being by weight: 35

degree sufficient for the amount of plasticizer EXAMPLE I that it wouldordinarily be desirable to employ, and are practically non-volatile atordinary at- Coating composition mospheric pressures and temperatures.

In carrying out the invention the plasticizer Ingredients Parts byweight40 may be incorporated with the halogen containing rubber derivative bymilling, rolling or working Amorphous rubber hydrochloride (viz, thematerials together in the absence of volatile 37? f) 10 10 solvents andmthe pr ence of n si oxide etldfii fi f..iiiiifii:3231;133:111: lot 10310% 108 100 or other basic stabilizers such as described in 4,5

Winkelmann Patent No. 2,046,986. Alternatively the materials may beincorporated with the aid of a quantity of mutual volatile solvent.More- C at ng composztzon over the materials may be incorporated in therubber prior to reaction with the halogen or Ingredients Partsby wei 50hydrohalogen.

The benzoates which are suitable plasticizers include butyl benzoylbenzoate, methyl benzoyl benzoate, ethyl benzoyl benzoate. Aparticularly 100 100 100 100 100 suitable compound for plasticizingvulcanized EXAMPLE II The above ingredients were milled and fluxed intoan intimate mixture and then molded and cured at 287 F. for twenty tosixty minutes. Tensile, modulus at 300%, P. & J. and shore hardness, andelongation tests on the molded products are shown in Tables I and II:

TABLE I A composition Mod. Ten- Elon- P. & Cure 800% sile gation set JShore 20' X 287 F 1670 197 12 12 97 30' X 287- 1360 377 23 16 95 x 287-1610 700 52 56 76 X 2871 1310 660 46 56 75 60' X 287 650 1250 610 44 58TABLE II B composition Mod. Ten- Elon- P. & Cure 300% sile gation Set JShow 20' x 287 F 2220 87 4 10 99 30 X 287. 1600 220 13 12 98 40 X 287-1300 1860 470 28 21 93 50' X 287. 1150 1750 567 37 41 83 60 x 287 11401350 427 24 41 81 The preparation of other vulcanized rubberhydrochloride compositions is described in detail in my copendingapplication Ser. No. 22,431 filed May 20, 1935.

A large number of esters of benzoyl benzoic acid have been tested asplasticizers for halogen containing rubber derivatives. The high boilingliquid esters and soft solids of the formula in which R is an alkyl suchas methyl, ethyl, propyl, butyl, amyl, hexyl, etc. and the benzoyl groupis in the ortho position, are the preferred plasticizers. However, thehigh boiling liquid and soft solid esters in which R may be an alkyl,aryl, or araryl and the benzoyl group is in the ortho, meta, or paraposition are also operable.

I claim:

1. A composition comprising a vulcanized rubber hydrochloride and anester of benzoyl benzoic acid.

2. A composition comprising a vulcanized rubber hydrochloride and anester of benzoyl benzoic acid, the benzoyl ester being present in amountof from about 10% to 100% by weight of the vulcanized rubberhydrochloride.

3. A composition comprising a vulcanized rubber hydrohalide and as aplasticizer therefor, butyl benzoyl benzoate.

HERBERT A. WINKEIMANN.

